Photoredox-Catalyzed Radical–Radical Cross-Coupling of Sulfonyl Chlorides with Trifluoroborate Salts

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(15), С. 11161 - 11172

Опубликована: Июль 25, 2023

Sulfones are widely found in natural products and drug molecules. Here, we disclose a strategy for direct synthesis of sulfone compounds with diverse structures by visible-light-catalyzed radical-radical cross-coupling sulfonyl chlorides trifluoroborate salts. Allyl, benzyl, vinyl, aryl trifluoroborates can be successfully cross-coupled (hetero)aryl alkyl chlorides, respectively. This features redox neutrality, good substrate generality, simple operation, benign reaction conditions.

Язык: Английский

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TEMPO Mediated Cyclopropanols Ring Opening C−N Cross‐Coupling with Nitrogen Nucleophiles

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(10), С. 1678 - 1684

Опубликована: Апрель 28, 2023

Abstract A feasible and umpolung strategy for the synthesis of structurally diverse β ‐amino ketones has been achieved through TEMPO mediated C−N coupling cyclopropanols with nitrogen nucleophiles. Mechanism studies indicated that in situ generated enones derived from are key intermediates play multiple roles, including radical initiator, trapping reagent, a porter ‐hydrogen an base. This protocol features broad substrate scope, good scalability to excellent yields provides alternative complementary approach important ketone scaffolds under metal additive‐free conditions. magnified image

Язык: Английский

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Regio- and stereoselective manganese-catalyzed hydrosulfonylation of alkynes: facile access to Z-vinyl sulfones

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(20), С. 5164 - 5170

Опубликована: Янв. 1, 2023

We have reported a concise and complementary approach for the synthesis of high-selectivity ( Z )-vinyl sulfones via ligand-tuned metalloradical reactivity strategy.

Язык: Английский

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Manual Grinding and Sunlight Synergistically Promoted Sulfonylation of Alkenyl Sulfonium Salts with Sulfinic Acids

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 10, 2025

An environmentally friendly and practical method for the synthesis of various vinyl sulfones was developed through direct sulfonylation alkenyl sulfonium salts with sulfinic acids. The reaction effectively triggered by combined actions milling, sunlight, photocatalysts under solvent-free conditions, offering advantages such as a short time (5-10 min), room temperature, straightforward workup procedure. Preliminary mechanistic studies suggested that sulfonyl radical may be involved in this mechanophotocatalytic transformation process.

Язык: Английский

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Nickel-Catalyzed Suzuki–Miyaura Coupling in Water for the Synthesis of 2-Aryl Allyl Phosphonates and Sulfones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2448 - 2458

Опубликована: Янв. 26, 2024

An operationally simple and green protocol using a NiSO4·6H2O/cationic 2,2′-bipyridyl ligand system as water-soluble catalyst for the coupling of arylboronic acids with (2-haloallyl)phosphonates (2-haloallyl)sulfones in water under air was developed. The reaction performed at 120 °C (2 mmol) or sulfones (1 presence 5 mol % Ni catalytic basic aqueous solution 1 h, giving corresponding 2-aryl allyl phosphonates good to excellent yields. This features use an abundant transition metal exhibits high functional group tolerance, rendering it eco-friendly procedure.

Язык: Английский

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Transition metal-free [3 + 3] annulation of cyclopropanols with β-enamine esters to assemble nicotinate derivatives

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(45), С. 8984 - 8988

Опубликована: Янв. 1, 2023

A metal-free and efficient approach for the synthesis of structurally important nicotinates through 4-HO-TEMPO-mediated [3 + 3] annulation cyclopropanols with β-enamine esters is presented. This protocol features high atom efficiency, green waste, simple operation broad substrate scope. Moreover, experiments gram-scale recovery oxidants make this strategy more sustainable practical.

Язык: Английский

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Copper-catalyzed 4-HO-TEMPOH mediated phosphorylation of alkenes

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(25), С. 5171 - 5175

Опубликована: Янв. 1, 2023

A copper-catalyzed unprotected hydroxylamine mediated phosphorylation of alkenes furnished structurally important ( E )-alkenylphosphine oxides under mild reaction conditions with good functional group tolerance and excellent regioselectivity.

Язык: Английский

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